US9525144B2 - Organic light-emitting diode - Google Patents

Organic light-emitting diode Download PDF

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US9525144B2
US9525144B2 US14/016,030 US201314016030A US9525144B2 US 9525144 B2 US9525144 B2 US 9525144B2 US 201314016030 A US201314016030 A US 201314016030A US 9525144 B2 US9525144 B2 US 9525144B2
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Sun-young Lee
Yoon-Hyun Kwak
Bum-Woo Park
Jong-Won Choi
Wha-Il CHOI
So-Yeon Kim
Ji-Youn Lee
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Samsung Display Co Ltd
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    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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    • H10K50/00—Organic light-emitting devices
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    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H10K50/156—Hole transporting layers comprising a multilayered structure

Definitions

  • One or more embodiments of the present invention relate to an organic light-emitting diode.
  • OLEDs Organic light-emitting diodes
  • OLEDs which are self-emitting diodes, have advantages such as wide viewing angles, excellent contrast, quick response, high brightness, excellent driving voltage characteristics, and can provide multicolored images.
  • a typical OLED has a structure including a substrate; and an anode, a hole transport layer (HTL), an second electrode (EML), an electron transport layer (ETL), and a cathode sequentially stacked on the substrate.
  • the HTL, the EML, and the ETL are organic thin films formed of organic compounds.
  • An operating principle of an OLED having the above-described structure is as follows.
  • aspects of one or more embodiments of the present invention are directed toward an organic light-emitting diode having a novel structure.
  • an organic light-emitting device includes: a substrate; a first electrode on the substrate; a second electrode opposite to the first electrode; an emission layer between the first electrode and the second electrode; a hole migration transfer region between the first electrode and the emission layer; and an electron migration region between the emission layer and the second electrode,
  • the hole migration region includes a first compound represented by Formula 1, and at least one of the hole migration region and the emission layer includes a second compound represented by Formula 100 below:
  • Ar 101 and Ar 102 are, each independently, a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 2 -C 10 heterocyclooalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 2 -C 10 heterocyclooalkenylene group, a substituted or unsubstituted C 6 -Cho arylene group, or a substituted or unsubstituted C 2 -C 60 heteroarylene group;
  • xa and xb are, each independently, an integer from 0 to 5;
  • R 101 and R 109 are, each independently, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, or a substituted or unsubstituted C 2 -C 60 heteroaryl group; and
  • R 102 to R 108 , and R 111 to R 119 are, each independently, a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstit
  • R 56 and R 57 are linked to each other to form a substituted or unsubstituted C 3 -C 60 cyclic moiety, or a substituted or unsubstituted C 2 -C 60 heterocyclic moiety, and R 51 to R 55 and R 58 to R 60 are, each independently, a substituent represented by —(Ar 51 ) q —(Ar 61 ), or
  • R 58 and R 59 are linked to each other to form a substituted or unsubstituted C 3 -C 60 cyclic moiety, or a substituted or unsubstituted C 2 -C 60 heterocyclic moiety, and R 51 to R 57 and R 60 are, each independently, a substituent represented by —(Ar 51 ) q —(Ar 61 );
  • Ar 50 and Ar 51 are, each independently, a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 2 -C 10 heterocyclooalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a C 2 -C 10 heterocyclooalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, or a substituted or unsubstituted C 2 -C 60 heteroarylene group;
  • Ar 60 and Ar 61 are, each independently, selected from among a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 2 -C 10
  • p and q are, each independently, an integer from 0 to 5.
  • FIG. 1 is a schematic view of a structure of an organic light-emitting diode according to an embodiment of the present invention
  • FIG. 2 is a schematic view of a structure of an organic light-emitting diode according to another embodiment of the present invention.
  • FIG. 3 is a schematic view of a structure of an organic light-emitting diode according to another embodiment of the present invention.
  • an organic light emitting diode 10 has a structure including a substrate 11 , a first electrode 12 , a hole migration region 13 , an emission layer (EML) 15 , an electron migration region 17 , and a second electrode 19 that are sequentially stacked on one another.
  • EML emission layer
  • the substrate 11 may be any substrate that is used in existing organic light-emitting diodes.
  • the substrate 11 may be a glass substrate or a transparent plastic substrate with strong mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.
  • the first electrode 12 may be formed by depositing or sputtering a first electrode-forming material on the substrate 11 .
  • a material having a high work function may be used as the first electrode-forming material to facilitate hole injection.
  • the first electrode 12 may be a reflective electrode or a transmission electrode. Transparent and conductive materials (such as ITO, IZO, SnO 2 , or ZnO) may be used to form the first electrode 12 .
  • the first electrode 12 may be formed as a reflective electrode using magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or the like.
  • the first electrode 12 may have a single-layer structure or a multi-layer structure including at least two layers.
  • the first electrode 12 may have a three-layered structure of ITO/Ag/ITO, but is not limited thereto.
  • the first electrode 12 may be a hole-injecting electrode (anode).
  • the second electrode 19 is disposed opposite to the first electrode 12 .
  • the second electrode 19 may be a cathode, which is an electron injecting electrode.
  • a metal for forming the second electrode 19 may be a metal, an alloy, an electrically conductive compound, which have a low-work function, or a mixture thereof.
  • the second electrode 19 may be formed of lithium (Li), magnesium (Mg), aluminum (Al), aluminum (Al)-lithium (Li), calcium (Ca), magnesium (Mg)-indium (In), magnesium (Mg)-silver (Ag), or the like, and may be formed as a thin film type transmission electrode.
  • the transmission electrode may be formed of indium tin oxide (ITO) or indium zinc oxide (IZO).
  • the EML 15 is disposed between the first electrode 12 and the second electrode
  • the hole migration region 13 is disposed between the first electrode 12 and the EML 15
  • the electron migration region 17 is disposed between the EML 15 and the second electrode 19 .
  • holes are injected through the first electrode 12 to migrate to the EML 15 through the hole migration region 13 , while electrons are injected through second electrode 19 to migrate to the EML 15 through the electron migration region 17 .
  • the holes and electrons recombine in the EML 15 to generate excitons. When the excitons drop from an excited state to a ground state, light is emitted.
  • the hole migration region 13 may include at least one layer. That is, the hole migration region 13 may have a single-layered structure or a laminated structure of at least two layers.
  • the electron migration region 17 may include at least one layer. That is, the electron migration region 17 may have a single-layered structure or a laminated structure of at least two layers.
  • the hole migration region 13 includes a first compound represented by Formula 1 below, and at least one of the hole migration region 13 and the EML 15 includes a second compound represented by Formula 100 below.
  • Ar 101 and Ar 102 may be, each independently, a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 2 -C 10 heterocyclooalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 2 -C 10 heterocyclooalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, or a substituted or unsubstituted C 2 -C 60 heteroarylene group.
  • Ar 101 and Ar 102 may be, each independently, selected from a substituted or unsubstituted phenylene group, a substituted or unsubstituted pentalenylene group, a substituted or unsubstituted indenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted azulenylene group, a substituted or unsubstituted heptalenylene group, a substituted or unsubstituted indacenylene group, a substituted or unsubstituted acenaphthylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted spiro-fluorenylene group, a substituted or unsubstituted phenalenylene group, a substituted or unsubstituted phenanthrenylene group, a substituted or
  • Ar 101 and Ar 102 in Formula 1 may be, each independently, represented by one of Formulae 3-1 to 3-24:
  • Y 1 may be O, S, C(R 21 )(R 22 ), or N(R 23 ).
  • Z 1 , Z 2 , and R 21 to R 23 may be, each independently, selected from among,
  • a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof;
  • a C 6 -C 20 aryl group and a C 2 -C 20 heteroaryl group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfuorenyl group, a diphenylfluorenyl group, a carbazolyl group,
  • Q 11 to Q 15 are, each independently, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a C 6 -C 20 aryl group, or a C 2 -C 20 heteroaryl group).
  • Z 1 , Z 2 , and R 21 to R 23 may be, each independently, selected from among,
  • a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof;
  • a phenyl group a naphthyl group, an anthryl group, a fluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group;
  • Q 11 to Q 15 are, each independently, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfuorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, or an isoquinolinyl group), but are not limited thereto.
  • Ar 101 , Ar 102 , Ar 1 , and Ar 2 in Formula 1 may be, each independently, represented by one of Formulae 4-1 to 4-7 below, but are not limited thereto:
  • xa indicates number of Ar 101 s
  • xb indicates number of Ar 102 s
  • xa and xb may be, each independently, an integer from 0 to 5.
  • xa and/or xb is 0, “carbazole” and/or “fluorene” in Formula 1 may be linked directly to “N”.
  • xa is 2 or greater
  • the at least two of Ar 101 s may be identical to or different from each other.
  • xb is 2 or greater, the at least two of Ar 102 s may be identical to or different from each other.
  • R 101 and R 109 may be, each independently, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, or a substituted or unsubstituted C 2 -C 60 heteroaryl group.
  • R 101 and R 109 may be, each independently, selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted pentalenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted azulenyl group, a substituted or unsubstituted heptalenyl group, a substituted or unsubstituted indacenyl group, a substituted or unsubstituted acenaphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spiro-fluorenyl group, a substituted or unsubstituted phenalenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or
  • R 101 and R 109 may be, each independently, represented by one of Formulae 5-1 to 5-22 below:
  • Y 2 may be O, S, C(R 25 )(R 26 ), or N(R 27 ).
  • Z 11 to Z 14 , and R 25 to R 27 may be, each independently, selected from among,
  • a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof;
  • a C 6 -C 20 aryl group and a C 2 -C 20 heteroaryl group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group C 2 -C 60 alkynyl group, C 1 -C 60 alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfuorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarb
  • Q 11 to Q 15 are, each independently, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a C 6 -C 20 aryl group, or a C 2 -C 20 heteroaryl group).
  • Z 11 to Z 14 , and R 25 to R 27 in Formulae 5-1 to 5-22 may be, each independently, selected from among,
  • a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof;
  • a phenyl group a naphthyl group, an anthryl group, a fluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group;
  • Q 11 to Q 15 are, each independently, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfuorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, or an isoquinolinyl group), but are not limited thereto.
  • R 101 in Formula 1 may be a group represented by one of Formulae 6-1 to 6-8 below
  • R 109 in Formula 1 may be a group represented by one of Formulae 6-1 to 6-11 below:
  • Z 11a to Z 11c may be defined the same as Z 11 described above, and R 25 , R 26 , Q 11 , and Q 12 may be defined the same as described above.
  • Z 11a to Z 11c , R 25 , and R 26 may be, each independently, selected from among,
  • a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof;
  • Q 11 and Q 12 may be, each independently, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfuorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, or an isoquinolinyl group.
  • R 111 and R 112 in Formula 1 may be, each independently, selected from among
  • a C 1 -C 20 alkyl group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof;
  • R 56 and R 57 may be linked to each other to form a substituted or unsubstituted C 3 -C 60 cyclic moiety, or a substituted or unsubstituted C 2 -C 60 heterocyclic moiety, and R 51 to R 55 and R 58 to R 60 may be, each independently, a substituent represented by —(Ar 51 ) q —(Ar 61 ).
  • R 58 and R 59 may be linked to each other to form a substituted or unsubstituted C 3 -C 60 cyclic moiety, or a substituted or unsubstituted C 2 -C 60 heterocyclic moiety, and R 51 to R 57 and R 60 may be, each independently, a substituent represented by —(Ar 51 ) q —(Ar 61 ).
  • the second compound may be a compound represented by Formula 100A or 100B below:
  • Ar 50 , Ar 60 , p, and R 51 to R 60 may be the same as those described above.
  • P ring and Q ring may be, each independently, selected from among,
  • benzene naphthalene, fluorene, carbazole, dibenzofuran, and dibenzothiophene, substituted with one selected from among
  • a C 1 -C 20 alkyl group and a C 1 -C 60 alkoxy group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof,
  • Q 11 and Q 12 may be, each independently, a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, or an isoquinolinyl group).
  • R 51 to R 54 in Formulae 100A and 100B may all be hydrogen atoms.
  • the second compound may be a compound represented by one of Formulae 100A-1 to 100A-8 and 100B-1 to 100B-9, but is not limited thereto:
  • R 51 to R 60 , Ar 50 , Ar 60 , and p may be the same as those described above;
  • X 12 may be O, S, C(R 71 )(R 72 ), or N(R 73 );
  • R 61 , R 62 , and R 71 to R 73 may be, each independently, selected from among
  • a C 1 -C 60 alkyl group a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group, substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof,
  • Q 11 and Q 12 may be, each independently, a C 6 -C 60 aryl group or a C 2 -C 60 heteroaryl group
  • Q 13 to Q 15 are, each independently, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a C 6 -C 60 aryl group, or a C 2 -C 60 heteroaryl group
  • Q 11 and Q 12 may be, each independently, a C 6 -C 60 aryl group or a C 2 -C 60 heteroaryl group
  • Q 13 to Q 15 are, each independently, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a C 6 -C 60 aryl group, or a C 2 -C 60 heteroaryl group
  • R 61 , R 62 , and R 71 to R 73 may be, each independently, selected from among
  • a C 1 -C 20 alkyl group and a C 1 -C 60 alkoxy group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof;
  • Q 11 and Q 12 may be, each independently, a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, or an isoquinolinyl group; and Q 13 to Q 15 may be, each independently, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthryl group,
  • Ar 50 and Ar 51 may be, each independently, selected from a substituted or unsubstituted phenylene group, a substituted or unsubstituted pentalenylene group, a substituted or unsubstituted indenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted azulenylene group, a substituted or unsubstituted heptalenylene group, a substituted or unsubstituted indacenylene group, a substituted or unsubstituted acenaphthylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted spiro-fluorenylene group, a substituted or unsubstituted phenalenylene group, a substituted or unsubstituted phenanthrenylene group, a substituted or unsubsti
  • Ar 50 and Ar 51 may be, each independently, selected from among
  • Ar 50 and Ar 51 may be, each independently, selected from among groups represented by Formulae 102-1 to 102-5:
  • Z 21 and Z 22 may be, each independently, selected from among a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group,
  • f 1 may be an integer from 1 to 3;
  • f 2 may be an integer from 1 to 4;
  • * indicates a binding site of a core in Formula 1, or a binding site of other Ar 50 or Ar 51 spaced from the core of Formula 1;
  • *′ indicates a binding site of Ar 50 or Ar 51 spaced from the core of Formula 1, or a binding site of Ar 60 or Ar 61 .
  • Ar 60 and Ar 61 may be, each independently, selected from among a substituted or unsubstituted phenyl group, a substituted or unsubstituted pentalenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted azulenyl group, a substituted or unsubstituted heptalenyl group, a substituted or unsubstituted indacenyl group, a substituted or unsubstituted acenaphtyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spiro-fluorenyl group, a substituted or unsubstituted phenalenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or un
  • Ar 60 and Ar 61 in Formula 100 may be, each independently, selected from among groups represented by Formulae 103-1 to 103-16:
  • Y 21 may be O, S, C(Z 41 )(Z 42 ), or N(Z 43 );
  • Z 31 , Z 32 , and Z 41 to Z 43 may be, each independently, selected from among a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group,
  • Q 21 and Q 22 may be, each independently, selected from among a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group;
  • embodiments of the present invention are not limited thereto.
  • “p” in —(Ar 50 ) p —(Ar 60 ) indicates the number of Ar 50 s, and may be an integer from 0 to 5. When p is 0, Ar 60 may be directly linked to nitrogen in Formula 100. When p is 2 or greater, the two or more Ar 50 s may be identical to or differ from each other.
  • “q” in —(Ar 51 ) q —(Ar 61 ) indicates the number of Ar 51 s, and may be an integer from 0 to 5. When q is 0, Ar 61 may be directly linked to the core of Formula 100. When q is 2 or greater, the two or more Ar 51 s may be identical to or differ from each other.
  • the first compound may be a compound represented by Formula 1A, 1B, or 1C below:
  • substitutents in Formulae 1A, 1B, and 1C may be the same as those described above.
  • Ar 101 and Ar 102 may be, each independently, a group represented by one of Formulae 3-1 to 3-24;
  • xa and xb may be, each independently, 1 or 2;
  • R 101 and R 109 may be, each independently, a group represented by one of Formulae 5-1 to 5-22;
  • R 111 and R 112 may be, each independently, one selected from among
  • a C 1 -C 20 alkyl group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof,
  • R 102 to R 108 and R 113 to R 119 may be, each independently, selected from among
  • a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof;
  • Ar 101 and Ar 102 may be, each independently, a group represented by one of Formulae 4-1 to 4-7;
  • xa and xb may be, each independently, 1 or 2;
  • R 101 may be a group represented by one of Formulae 6-1 to 6-8;
  • R 109 may be a group represented by one of Formulae 6-1 to 6-11;
  • R 111 and R 112 may be, each independently, one selected from among
  • a C 1 -C 20 alkyl group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof;
  • R 102 to R 108 and R 113 to R 119 may be hydrogen atoms.
  • the second compound may be represented by Formula 100A-HLT or 100B-HLT.
  • P ring and Q ring may be, each independently, selected from among
  • benzene naphthalene, fluorene, carbazole, dibenzofuran, and dibenzothiophene, substituted with at least one selected from among
  • a C 1 -C 20 alkyl group and a C 1 -C 60 alkoxy group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof,
  • Q 11 and Q 12 are, each independently, a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, or an isoquinolinyl group);
  • Ar 50 and Ar 51 may be, each independently, selected from among
  • p and q may be, each independently, 0, 1, or 2;
  • Ar 61 , Q 21 , and Q 22 may be, each independently, selected from among a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group.
  • the second compound may be a compound represented by Formula 100A-H1 or 100B-H1 below:
  • P ring and Q ring may be, each independently, selected from among
  • benzene naphthalene, fluorene, carbazole, dibenzofuran, and dibenzothiophene, substituted with at least one selected from among
  • a C 1 -C 20 alkyl group and a C 1 -C 60 alkoxy group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof,
  • Q 11 and Q 12 may be, each independently, a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, or an isoquinolinyl group);
  • Ar 50 and Ar 51 may be, each independently, selected from among
  • p and q may be, each independently, 0, 1, or 2;
  • Z 21 and Z 22 may be, each independently, selected from among a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group,
  • f1 and f2 may be, each independently, 0, 1, or 2;
  • Ar 60 and Ar 61 may be, each independently, selected from among groups represented by Formulae 103-1 to 103-16.
  • the first compound of Formula 1 may be one of Compounds 1-1 to 1-19 below, but is not limited thereto:
  • the second compound of Formula 100 may be one of Compounds 2-1 to 2-30 below, but is not limited thereto:
  • Q 13 to Q 15 may be, each independently, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a C 6 -C 60 aryl group, or a C 2 -C 60 heteroaryl group), but not limited thereto.
  • the first compound of Formula 1 above has good charge (hole) transporting ability.
  • the second compound of Formula 100 above has good charge (hole) transporting ability, good light-emitting ability, and has a high band gap energy between the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO), and thus allows easy energy level adjustment.
  • the organic light-emitting diode 10 may have a low driving voltage, a high luminance, a high efficiency, and a long lifetime.
  • the first compound of Formula 1 and the second compound of Formula 100 may be both in the hole migration region 13 .
  • the first compound of Formula 1 above may be in the hole migration region 13
  • the second compound of Formula 100 above may be in the EML 15 .
  • the first compound of Formula 1 above and the second compound of Formula 100 above may be both in the hole migration region 13 , and the second compound of Formula 100 above may be in the EML 15 .
  • the second compound in the hole migration region 13 and the second compound in the EML 15 may be the same or different from each other.
  • FIG. 2 is a schematic view of a structure of an organic light-emitting diode 20 according to another embodiment of the present invention.
  • the organic light emitting diode 20 has a structure including a substrate 21 , a first electrode 22 , a hole migration region 23 , an emission layer (EML) 25 , an electron migration region 27 , and a second electrode 29 that are sequentially stacked on one another.
  • the hole migration region 23 includes a hole injection layer (HIL) 23 A, a first hole transport layer (HTL) 23 B- 1 , and a second HTL 23 B- 2 that are sequentially stacked on the first electrode 22 .
  • the electron migration region 27 includes an electron transport layer (ETL) 27 A and an electron injection layer (EIL) 27 B that are sequentially stacked on the EML 25 .
  • ETL electron transport layer
  • the above-detailed descriptions of the substrate 11 , the first electrode 12 , and the second electrode 19 may be referred to as detailed descriptions of the substrate 21 , the first electrode 22 , and the second electrode 29 of FIG. 2 .
  • the HIL 23 A may be formed on the first electrode 22 by any of a variety of methods, including vacuum deposition, spin coating, casting, and Langmuir-Blodgett (LB) deposition.
  • vacuum deposition spin coating, casting, and Langmuir-Blodgett (LB) deposition.
  • vacuum deposition conditions may vary according to the compound that is used to form the HIL 23 A, and the desired structure and thermal properties of the HIL 23 A to be formed.
  • vacuum deposition may be performed at a temperature of about 100° C. to about 500° C., a pressure of about 10 ⁇ 8 torr to about 10 ⁇ 3 torr, and a deposition rate of about 0.01 to about 100 ⁇ /sec.
  • the deposition conditions are not limited thereto.
  • the coating conditions may vary according to the compound that is used to form the HIL 23 A, and the desired structure and thermal properties of the HIL 23 A to be formed.
  • the coating rate may be in the range of about 2000 rpm to about 5000 rpm
  • a temperature at which heat treatment is performed to remove a solvent after coating may be in the range of about 80° C. to about 200° C.
  • the coating conditions are not limited thereto.
  • Non-limiting examples of materials for the HIL 23 A are N,N′-diphenyl-N,N′-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4′-diamine (DNTPD), a phthalocyanine compound (such as copperphthalocyanine), 4,4′,4′′-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine (NPB), TDATA, 2-TNATA, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonicacid (Pani/CSA), and polyaniline)/poly(4
  • the thickness of the HIL 23 A may be from about 100 ⁇ to about 10000 ⁇ , and in some embodiments, may be from about 100 ⁇ to about 1000 ⁇ . When the thickness of the HIL 23 A is within these ranges, the HIL 23 A may have good hole injecting ability without a substantial increase in driving voltage.
  • a first HTL 23 B- 1 may be formed on the HIL 23 A by using any of a variety of methods, for example, vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, or the like.
  • the conditions for deposition and coating may be similar to those for the formation of the HIL 23 A, although the conditions for the deposition and coating may vary depending on the material that is used to form the first HTL 23 B- 1 .
  • the first HTL 23 B- 1 may be formed using the first compound represented by Formula 1 above.
  • the above-detailed description of Formula 1A above may be referred to here.
  • a material for the first HTL 23 B- 1 may be one of Compounds 1-1 to 1-19 above.
  • a second HTL 23 B- 2 may be formed on the first HIL 23 B- 1 by using any of a variety of methods, for example, vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, or the like.
  • the conditions for deposition and coating may be similar to those for the formation of the HIL 23 A, although the conditions for the deposition and coating may vary depending on the material that is used to form the second HTL 23 B- 2 .
  • a material for the second HTL 23 B- 2 may be a second compound represented by Formula 100 above.
  • the above-detailed description of Formula 100 above may be referred to here.
  • the second HTL 23 B- 2 may include a second compound of Formula 100A-HLT or 100B-HLT.
  • the above-detailed descriptions of Formulae 100A-HLT and 100B-HLT may be referred to here.
  • the second compound may be Compound 2-1 or 2-27, but is not limited thereto.
  • a sum (total) of thicknesses of the first HTL 23 B- 1 and the second HTL 23 B- 2 may be from about 50 ⁇ to about 2000 ⁇ , and in some embodiments, from about 100 ⁇ to about 1500 ⁇ . In one embodiment, when the sum of thicknesses of the first HTL 23 B- 1 and the second HTL 23 B- 2 is within these ranges, the first HTL 23 B- 1 and second HTL 23 B- 2 have satisfactory hole transporting ability without a substantial increase in driving voltage.
  • a thickness ratio of the first HTL 23 B- 1 to the second HTL 23 B- 2 may be from about 1:9 to about 9:1, and in some embodiments, from about 3:7 to about 7:3, but is not limited thereto.
  • At least one of the HIL 23 A, the first HTL 23 B- 1 , and the second HTL 23 B- 2 may further include a charge-generating material, in addition to the above-described materials, to improve conductivity of the layers.
  • the charge-generating material may be, for example, a p-dopant.
  • the p-dopant may be one of quinine derivatives, metal oxides, and compounds with a cyano group, but are not limited thereto.
  • Non-limiting examples of the p-dopant are quinone derivatives such as tetracyanoquinonedimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ), or the like; metal oxides such as tungsten oxide, molybdenum oxide, or the like; and cyano-containing compounds such as Compound 200 below.
  • the charge-generating material may be homogeneously dispersed or inhomogeneously distributed in at least one of the HIL 23 A, the first HTL 23 B- 1 and the second HTL 23 B- 2 .
  • the charge-generating material may be present in any form.
  • the EML 25 may be formed on the second HTL 23 B- 2 by using vacuum deposition, spin coating, casting, LB deposition, or the like.
  • the deposition and coating conditions may be similar to those for the formation of the HIL 23 A, though the conditions for deposition and coating may vary depending on the material that is used to form the EML 25 .
  • the EML 25 may include a host and a dopant.
  • Non-limiting examples of the host are Alq 3 , 4,4′-N,N′-dicarbazole-biphenyl (CBP), poly(n-vinylcarbazole) (PVK), 9,10-di(naphthalene-2-yl)anthracene (ADN), TCTA, 1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBI), 3-tert-butyl-9,10-di-2-naphthylanthracene (TBADN), E3, distyrylarylene (DSA), dmCBP (see a formula below), and Compounds 501 to 509 below.
  • CBP 4,4′-N,N′-dicarbazole-biphenyl
  • PVK poly(n-vinylcarbazole)
  • ADN 9,10-di(naphthalene-2-yl)anthracene
  • TCTA 1,3,5-tris(N
  • an anthracene-based compound represented by Formula 400 below may be used as the host.
  • Ar 111 and Ar 112 may be, each independently, a substituted or unsubstituted C 6 -C 60 arylene group;
  • Ar 113 to Ar 116 may be, each independently, a substituted or unsubstituted C 1 -C 10 alkyl group or a substituted or unsubstituted C 6 -C 60 aryl group;
  • g, h, i, and j may be, each independently, an integer from 0 to 4.
  • Ar 111 and Ar 112 in Formula 400 may be, each independently, selected from a phenylene group, a naphthylene group, a phenanthrenylene group, and a pyrenylene group; and a phenylene group, a naphthylene group, a phenanthrenylene group, a fluorenyl group, and a pyrenylene group, substituted with at least one of a phenyl group, a naphthyl group, and an anthryl group.
  • g, h, i, and j may be, each independently, 0, 1, or 2.
  • Ar 113 to Ar 116 in Formula 400 may be, each independently, selected from
  • a C 1 -C 10 alkyl group substituted with at least one of a phenyl group, a naphthyl group, and an anthryl group;
  • a phenyl group a naphthyl group, an anthryl group, a pyrenyl group, a phenanthrenyl group and a fluorenyl group;
  • anthracene-based compound of Formula 400 above may be one of the compounds represented by the following formulae, but is not limited thereto:
  • an anthracene-based compound represented by Formula 401 below may be used as the host.
  • Ar 122 to Ar 125 in Formula 401 above may be defined as described above in conjunction with Ar 113 of Formula 400, and thus detailed descriptions thereof will not be provided here.
  • Ar 126 and Ar 127 in Formula 401 above may be, each independently, a C 1 -C 10 alkyl group, for example, a methyl group, an ethyl group, or a propyl group.
  • k and l may be, each independently, an integer from 0 to 4, for example, 0, 1, or 2.
  • anthracene compound of Formula 401 above may be one of the compounds represented by the following formulae, but is not limited thereto:
  • the EML 25 may include the second compound represented by Formula 100 above as a host.
  • the EML 25 includes the second compound of Formula 100 as a host, the host in the EML 25 and the material of the second HTL 23 B- 2 may be the same or differ from each other.
  • the second electrode may be patterned into a red second electrode, a green second electrode, and a blue second electrode.
  • the EML 23 may include a red second electrode, a green second electrode, and/or a blue second electrode that are stacked upon one another to emit white light, but is not limited thereto.
  • the dopant in the EML 25 may be a suitable dopant.
  • Non-limiting examples of the blue dopant are compounds represented by the following formulae.
  • red dopant examples are compounds represented by the following formulae.
  • the red dopant may be DCM or DCJTB, which will be described later.
  • green dopant are compounds represented by the following formulae.
  • the green dopant may be C545T represented below.
  • Non-limiting examples of the dopant that may be used in the EML are complexes represented by the following formulae:
  • Non-limiting examples of the dopant that may be used in the EML 25 are Os complexes represented by the following formulae:
  • the amount of the dopant may be, but is not limited to, from about 0.01 to about 15 parts by weight based on 100 parts by weight of the host.
  • a thickness of the EML 25 may be from about 100 ⁇ to about 1000 ⁇ , and in some embodiments, may be from about 200 ⁇ to about 600 ⁇ . In one embodiment, when the thickness of the EML 25 is within these ranges, the EML 25 has improved light-emitting ability without a substantial increase in driving voltage.
  • an ETL 27 A may be formed on the EML 25 using any of a variety of methods, such as vacuum deposition, spin coating, casting, or the like.
  • the deposition and coating conditions may be similar to those for the formation of the HIL 23 A, though the deposition and coating conditions may vary depending on the material that is used to form the ETL 23 A.
  • a material for forming the ETL 27 A may be any suitable material that can stably transport electrons injected from the second electrode 29 .
  • Non-limiting examples of materials for forming the ETL are a quinoline derivative, such as tris(8-quinolinorate)aluminum (Alq3), TAZ, BAIq, beryllium bis(benzoquinolin-10-olate (Bebq 2 ), 9,10-di(naphthalene-2-yl)anthracene (ADN), Compound 201, and Compound 202, but are not limited thereto.
  • a quinoline derivative such as tris(8-quinolinorate)aluminum (Alq3), TAZ, BAIq, beryllium bis(benzoquinolin-10-olate (Bebq 2 ), 9,10-di(naphthalene-2-yl)anthracene (ADN), Compound 201, and Compound 202, but are not limited thereto.
  • the thickness of the ETL 27 A may be from about 100 ⁇ to about 1,000 ⁇ , and in some embodiments, may be from about 150 ⁇ to about 500 ⁇ . In one embodiment, when the thickness of the ETL 27 A is within these ranges, the ETL 237 A has satisfactory electron transporting ability without a substantial increase in driving voltage.
  • the ETL 27 A may further include a metal-containing material, in addition to such an electron transporting organic material as described above.
  • the metal-containing material may include a lithium (Li) complex.
  • Li lithium
  • Non-limiting examples of the Li complex are lithium quinolate (LiQ) and Compound 203 below:
  • an EIL 27 B which facilitates injection of electrons from the anode, may be formed on the ETL 27 A. Any suitable electron-injecting material may be used to form the EIL 27 B.
  • Non-limiting examples of materials for forming the EIL 27 B are LiF, NaCl, CsF, Li 2 O, and BaO.
  • the deposition and coating conditions for forming the EIL 27 B may be similar to those for the formation of the HIL 23 A, though the deposition and coating conditions may vary according to the material that is used to form the EIL 27 B.
  • the thickness of the EIL 28 B may be from about 1 ⁇ to about 100 ⁇ , and in some embodiments, may be from about 3 ⁇ to about 90 ⁇ . In one embodiment, when the thickness of the EIL 27 B is within these ranges, the EIL 27 B has satisfactory electron injection ability without a substantial increase in driving voltage.
  • the EML 25 may include the second compound of Formula 100 described above.
  • the EML 25 may include the second compound of Formula 100A-H1 or 100B-H1.
  • FIG. 3 is a schematic view of a structure of an organic light-emitting diode 30 according to another embodiment of the present invention.
  • the organic light emitting diode 30 has a structure including a substrate 31 , a first electrode 32 , a hole migration region 33 , an EML 35 , an electron migration region 37 , and a second electrode 39 that are sequentially stacked on one another.
  • the hole migration region 33 includes a HIL 33 A and a HTL 33 B that are sequentially stacked on the first electrode 32 .
  • the electron migration region 37 includes an ETL 37 A and an EIL 37 B that are sequentially stacked on the EML 35 .
  • the above-detailed descriptions of the substrate 21 , the first electrode 22 , the HIL 23 A, the ETL 27 A, the EIL 27 B, and the second electrode 29 may be referred to as detailed descriptions of the substrate 31 , the first electrode 32 , the HIL 33 A, the ETL 37 A, the EIL 38 B, and the second electrode 39 of FIG. 3 .
  • a material for the HTL 33 B may be a first compound represented by Formula 1 above.
  • the HTL 33 B may include a first compound of the Formula 1A, 1B, or 1C, wherein, in Formulae 1A, 1B and 1C, Ar 101 and Ar 102 may be, each independently, a group represented by one of Formulae 4-1 to 4-7; xa and xb may be, each independently, 1 or 2; R 101 may be a group represented by one of Formulae 6-1 to 6-8; R 109 may be a group represented by one of Formulae 6-1 to 6-11; R 111 and R 112 may be, each independently, one of a C 1 -C 20 alkyl group; a C 1 -C 20 alkyl group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group
  • a material for the HTL 33 B may be one of Compounds 1-1 to 1-19 above.
  • the thickness of the HTL 33 B may be from about 50 ⁇ to about 2000 ⁇ , and in some embodiments, may be from about 100 ⁇ to about 1500 ⁇ . In one embodiment, when the thickness of the HTL 33 B is within these ranges, the HTL 33 B may have satisfactory hole transporting ability without a substantial increase in driving voltage.
  • At least one of the HIL 33 A and the HTL 33 B may further include a charge-generating material as described above.
  • the EML 35 may include a host and a dopant, the host including a second compound represented by Formula 100 above.
  • the above-detailed description of Formula 100 above may be referred to here.
  • the EML 35 may include the second compound of Formula 100A-H1 or 100B-H1 as a host.
  • the above-detailed descriptions of Formulae 100A-H1 and 100B-H1 may be referred to here.
  • the EML 35 may include Compound 2-5, 2-7, 2-23, or 2-30 as a host, but is not limited thereto.
  • a buffer layer may be further disposed between the second HTL 23 B- 2 and the EML 25 of FIG. 2 , or between the HTL 33 B and the EML 35 of FIG. 3 in order to compensate for an optical resonance distance according to the wavelength of light emitted from the EML 25 or 35 for higher efficiency.
  • the buffer layer may include a suitable hole injection material, a suitable hole transporting material, the first compound of Formula 1 above, or the second compound of Formula 100 above.
  • a hole blocking layer may be disposed between the EML 25 and the ETL 27 A of FIG. 2 , or between the EML 35 and the ETL 37 A of FIG. 3 , in order to prevent diffusion of triplet exitons or holes into the ETL 27 A or 37 A.
  • HBL hole blocking layer
  • the conditions for deposition and coating may be similar to those for the formation of the HIL, although the conditions for deposition and coating may vary according to the material that is used to form the HBL.
  • Any suitable hole-blocking material may be used.
  • Non-limiting examples of hole-blocking materials are oxadiazole derivatives, triazole derivatives, and phenanthroline derivatives.
  • bathocuproine (BCP) represented by the following formula may be used as a material for forming the HBL.
  • the thickness of the HBL may be from about 20 ⁇ to about 1000 ⁇ , and in some embodiments, may be from about 30 ⁇ to about 300 ⁇ . In one embodiment, when the thickness of the HBL is within these ranges, the HBL has improved hole blocking ability without a substantial increase in driving voltage.
  • the HIL 23 A of FIG. 2 and/or the HIL 33 A of FIG. 3 may not be included.
  • embodiments of the present invention are not limited thereto, and may include any of a variety of structures.
  • the unsubstituted C 1 -C 60 alkyl group may be a linear or branched C1-C60 alkyl group, including a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a pentyl group, an iso-amyl group, and a hexyl group.
  • the substituted C 1 -C 60 alkyl group may include at least one substituent selected from among a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group; a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group, substituted with at least one of a deuterium atom, a
  • the unsubstituted C 1 -C 60 alkoxy group (or a C 1 -C 60 alkoxy group) is represented by —OA (where A indicates a C 1 -C 60 alkyl group as described above), and may be, for example, a methoxy group, an ethoxy group, or an isopropoxy group. At least one hydrogen atoms of these alkyl groups may be substituted with those substituents described above in conduction with the substituted C 1 -C 60 alkyl group.
  • the unsubstituted C 2 -C 60 alkenyl group refers to a C 2 -C 60 alkyl group as described above with at least one carbon double bond in the middle or terminal thereof.
  • the alkenyl group are an ethenyl group, a propenyl group, a butenyl group, and the like.
  • At least one hydrogen atom in the unsubstituted C 2 -C 60 alkenyl group may be substituted with those substituents described above in conjunction with the substituted C 1 -C 60 alkyl group.
  • the unsubstituted C 2 -C 60 alkynyl group is a C 2 -C 60 alkyl group having at least one carbon-carbon triple bond in the center or at a terminal thereof.
  • Examples of the unsubstituted C 2 -C 60 alkynyl group are an ethenyl group, a propynyl group, and the like.
  • At least one hydrogen atom in the alkynyl group may be substituted with those substituents described above in conjunction with the substituted C 1 -C 60 alkyl group.
  • the unsubstituted C 6 -C 60 aryl group is monovalent carbocyclic aromatic system having 6 to 60 carbon atoms including at least one aromatic ring.
  • the unsubstituted C 6 -C 60 arylene group is a divalent group having a divalent carbocyclic aromatic system having 6 to 60 carbon atoms including at least one aromatic ring.
  • the aryl group and the arylene group may be fused to each other via a single bond.
  • At least one hydrogen atom in the aryl group and the arylene group may be substituted with those substituents described above in conjunction with the C 1 -C 60 alkyl group.
  • Examples of the substituted or unsubstituted C 6 -C 60 aryl group are a phenyl group, a C 1 -C 10 alkylphenyl group (e.g., an ethylphenyl group), a C 1 -C 10 alkylbiphenyl group (e.g., an ethylbiphenyl group), a halophenyl group (e.g., an o-, m- or p-fluorophenyl group and a dichlorophenyl group), a dicyanophenyl group, a trifluoromethoxyphenyl group, an o-, m- or p-tolyl group, an o-, m- or p-cumenyl group, a mesityl group, a phenoxyphenyl group, a ( ⁇ , ⁇ -dimethylbenzene)phenyl group, a (N,N′-dimethyl)aminoph
  • Examples of the substituted C 6 -C 60 aryl group may be inferred based on those of the unsubstituted C 6 -C 60 aryl group and the substituted C 1 -C 30 alkyl group described above.
  • Examples of the substituted or unsubstituted C 6 -C 60 arylene group may be inferred based on those examples of the substituted or unsubstituted C 6 -C 60 aryl group described above.
  • the unsubstituted C 2 -C 60 heteroaryl group is a monovalent group having at least one aromatic ring having at least one of the heteroatoms selected from the group consisting of N, O, P, and S.
  • the unsubstituted C 2 -C 60 heteroarylene group is a divalent group having at least one aromatic ring having at least one of the heteroatoms selected from the group consisting of N, O, P, and S.
  • the heteroaryl group and the heteroarylene group when they may be fused to each other via a single bond.
  • At least one hydrogen atom in the heteroaryl group and the heteroarylene group may be substituted with those substituents described with reference to the C 1 -C 60 alkyl group.
  • Examples of the unsubstituted C 2 -C 60 heteroaryl group are a pyrazolyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a pyridinyl group, a pyridazinyl group, a pyrimidinyl group, a triazinyl group, a carbazolyl group, an indolyl group, a quinolinyl group, an isoquinolinyl group, a benzoimidazolyl group, an imidazopyridinyl group and an imidazopyrimidinyl group.
  • Examples of the substituted or unsubstituted C 2 -C 50 heteroarylene group may be inferred based on those examples of the substituted or unsubstituted C 2 -C 60 arylene group described above.
  • the substituted or unsubstituted C 6 -C 60 aryloxy group indicates —OA 2 (where A 2 is a substituted or unsubstituted C 6 -C 60 aryl group described above).
  • the substituted or unsubstituted C 6 -C 60 arylthio group indicates —SA 3 (where A 3 is a substituted or unsubstituted C 6 -C 60 aryl group described above).
  • Intermediate 2-7-a was obtained in the same manner as in the synthesis of Intermediate 2-1-a, except that Intermediates SM2-7 and L2-5 instead of Intermediates SM2-1 and L2-1, respectively, were used.
  • Intermediate 2-27-c was obtained in the same manner as in the synthesis of Intermediate 2-23-c, except that Intermediates 2-27-b and L2-27 instead of Intermediates 2-23-b and L2-5, respectively, were used.
  • Intermediate 2-30-a was obtained in the same manner as in the synthesis of Intermediate 2-23-a, except that Intermediate SM2-30 and Compound b instead of Intermediate SM2-23 and Compound c, respectively, were used.
  • Intermediate 2-30-c was obtained in the same manner as in the synthesis of Intermediate 2-23-c, except that Intermediates 2-30-b and L2-30 instead of Intermediates 2-23-b and L2-5, respectively, were used.
  • a glass substrate with deposited ITO/Ag/ITO layers (70/1000/70 ⁇ ) was cut to a size of 50 mm ⁇ 50 mm ⁇ 0.5 mm and then ultrasonicated in isopropyl alcohol for five minutes and in pure water for five minutes, and then cleaned by irradiation of ultraviolet rays for 30 minutes and exposure to ozone.
  • the resulting glass substrate was loaded into a vacuum deposition device.
  • CBP host
  • PtOEP dopant
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 1-17 instead of Compound 1-8 was used to form the first HTL.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 1-19 instead of Compound 1-8 was used to form the first HTL, and Compound 2-27 instead of Compound 2-1 was used to form the second HTL.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that, instead of forming the first and second HTLs, a HTL having a thickness of about 1350 ⁇ was formed by depositing Compound 1-8 on the HIL, and Compound 2-7 instead of CBP was used as a host in forming the EML on the HTL
  • An organic light-emitting device was manufactured in the same manner as in Example 4, except that Compound 1-17 instead of Compound 1-8 was used to form the HTL.
  • An organic light-emitting device was manufactured in the same manner as in Example 4, except that Compound 1-19 instead of Compound 1-8 was used to form the HTL, and Compound 2-30 instead of Compound 2-7 was used as a host in forming the EML.
  • a glass substrate with deposited ITO/Ag/ITO layers (70 ⁇ /1000 ⁇ /70 ⁇ ) was cut to a size of 50 mm ⁇ 50 mm ⁇ 0.5 mm and then ultrasonicated in isopropyl alcohol and pure water each for five minutes, and then cleaned by irradiation of ultraviolet rays for 30 minutes and exposure to ozone.
  • the resulting glass substrate was loaded into a vacuum deposition device.
  • 2-TNATA was vacuum-deposited on the anode to form an HIL having a thickness of 600 ⁇ , and then Compound 1-8 was deposited on the HIL to form a HTL having a thickness of 1000 ⁇ .
  • Compound 2-5 (host) and Ir(ppy) 3 (dopant) were co-deposited in a weight ratio of about 91:9 on the HTL to form an EML having a thickness of about 250 ⁇ , followed by depositing BCP on the EML to form a HBL having a thickness of about 50 ⁇ .
  • BCP on the EML to form a HBL having a thickness of about 50 ⁇ .
  • LiF was deposited on the ETL to form an EIL having a thickness of about 10 ⁇ , followed by depositing Mg and Al in a weight ratio of about 90:10 on the EIL to form a cathode having a thickness of about 120 ⁇ , thereby manufacturing an organic light-emitting device (emitting green light).
  • An organic light-emitting device was manufactured in the same manner as in Example 7, except that Compound 1-17 instead of Compound 1-8 was used to form the HTL, and Compound 2-23 instead of Compound 2-5 was used as a host in forming the EML.
  • An organic light-emitting device was manufactured in the same manner as in Example 7, except that Compound 1-19 instead of Compound 1-8 was used to form the HTL, and Compound 2-23 instead of Compound 2-5 was used as a host in forming the EML.
  • An organic light-emitting device was manufactured in the same manner as in Example 7, except that Compound A represented by Formula A below, instead of Compound 1-8, was used to form the HTL, and CBP instead of Compound 2-5 was used as a host in forming the EML.
  • An organic light-emitting device was manufactured in the same manner as in Example 4, except that Compound A instead of Compound 1-8 was used to form the HTL, and CBP instead of Compound 2-7 was used as a host in forming the EML.
  • Driving voltages, current densities, luminances, emitting-light colors, efficiencies, and half-life spans (@10 mA/cm 2 ) of the organic light-emitting devices of Examples 1 to 8 and Comparative Examples 1 and 2 were measured using a PR650 (Spectroscan) Source Measurement Unit (available from Photo Research, Inc.). The results are shown in Tables 1 and 2 below.
  • LT 97 was evaluated as the time taken until a measured initial luminance (assumed as 100%) was reduced to 97% during driving at about 10 mA/cm 2 .
  • the organic light-emitting devices of Examples 1 to 6 were found to have lower driving voltages, higher luminances, higher efficiencies, higher color purities, and longer lifetimes than those of the organic light-emitting device of Comparative Example 2.
  • the organic light-emitting devices of Examples 6 to 9 were found to have lower driving voltages, higher luminances, higher efficiencies, higher color purities, and longer lifetimes than those of the organic light-emitting device of Comparative Example 1.
  • an organic light-emitting device (including a first compound of Formula 1 and a second compound of Formula 100) has a low driving voltage, high luminance, high efficiency, and long lifetime.

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